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Literature summary for 1.1.1.23 extracted from

  • Turtaut, F.; Lopez, M.; Ouahrani-Bettache, S.; Koehler, S.; Winum, J.Y.
    Oxo- and thiooxo-imidazo[1,5-c]pyrimidine molecule library: beyond their interest in inhibition of Brucella suis histidinol dehydrogenase, a powerful protection tool in the synthesis of histidine analogues (2014), Bioorg. Med. Chem. Lett., 24, 5008-5010.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
(3S)-3-amino-1-(2,4-difluorophenyl)-4-(1H-imidazol-4-yl)butan-2-one
-
Brucella suis
(3S)-3-amino-1-(4-bromophenyl)-4-(1H-imidazol-4-yl)butan-2-one
-
Brucella suis
(3S)-3-amino-1-(4-chlorophenyl)-4-(1H-imidazol-4-yl)butan-2-one
-
Brucella suis
(3S)-3-amino-1-([1,1'-biphenyl]-4-yl)-4-(1H-imidazol-4-yl)butan-2-one
-
Brucella suis
(3S)-3-amino-4-(1H-imidazol-4-yl)-1-(4-methylphenyl)butan-2-one
-
Brucella suis
(3S)-3-amino-4-(1H-imidazol-4-yl)-1-[4-(7-phenylhept-1-yn-1-yl)phenyl]butan-2-one
-
Brucella suis
(7S)-7-[(2,4-difluorophenyl)acetyl]-7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one
-
Brucella suis
(7S)-7-[(4-bromophenyl)acetyl]-7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one
-
Brucella suis
(7S)-7-[(4-chlorophenyl)acetyl]-7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one
-
Brucella suis
(7S)-7-[(4-methylphenyl)acetyl]-7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one
-
Brucella suis
(7S)-7-[([1,1'-biphenyl]-4-yl)acetyl]-7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one
-
Brucella suis
(7S)-7-[[4-(7-phenylhept-1-yn-1-yl)phenyl]acetyl]-7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one
-
Brucella suis
2-(2,4-difluorophenyl)-1-[(7S)-5-sulfanylidene-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidin-7-yl]ethan-1-one
-
Brucella suis
2-(4-bromophenyl)-1-[(7S)-5-sulfanylidene-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidin-7-yl]ethan-1-one
-
Brucella suis
2-(4-chlorophenyl)-1-[(7S)-5-sulfanylidene-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidin-7-yl]ethan-1-one
-
Brucella suis
2-(4-methylphenyl)-1-[(7S)-5-sulfanylidene-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidin-7-yl]ethan-1-one
-
Brucella suis
2-([1,1'-biphenyl]-4-yl)-1-[(7S)-5-sulfanylidene-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidin-7-yl]ethan-1-one
-
Brucella suis
2-[4-(7-phenylhept-1-yn-1-yl)phenyl]-1-[(7S)-5-sulfanylidene-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidin-7-yl]ethan-1-one
-
Brucella suis
methyl (7S)-5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate
-
Brucella suis
methyl (7S)-5-sulfanylidene-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate
-
Brucella suis
additional information synthesis of a family of oxo- and thioxo-imidazo[1,5-c]pyrimidines, potential enzyme inhibitors. These oxo- and thioxo-derivatives can improve dramatically the efficiency of the histidine protection pathway for the synthesis of histidine analogues, overview Brucella suis

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
L-histidinol + 2 NAD+ + H2O Brucella suis
-
L-histidine + 2 NADH + 3 H+
-
?

Organism

Organism UniProt Comment Textmining
Brucella suis
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
L-histidinol + 2 NAD+ + H2O
-
Brucella suis L-histidine + 2 NADH + 3 H+
-
?

Synonyms

Synonyms Comment Organism
HDH
-
Brucella suis

Cofactor

Cofactor Comment Organism Structure
NAD+
-
Brucella suis

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.005
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.14 Brucella suis 2-([1,1'-biphenyl]-4-yl)-1-[(7S)-5-sulfanylidene-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidin-7-yl]ethan-1-one
0.006
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.16 Brucella suis (3S)-3-amino-1-(4-bromophenyl)-4-(1H-imidazol-4-yl)butan-2-one
0.009
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.21 Brucella suis (3S)-3-amino-4-(1H-imidazol-4-yl)-1-[4-(7-phenylhept-1-yn-1-yl)phenyl]butan-2-one
0.01
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.19 Brucella suis (3S)-3-amino-1-(2,4-difluorophenyl)-4-(1H-imidazol-4-yl)butan-2-one
0.012
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.17 Brucella suis (3S)-3-amino-1-(4-chlorophenyl)-4-(1H-imidazol-4-yl)butan-2-one
0.012
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.20 Brucella suis (3S)-3-amino-1-([1,1'-biphenyl]-4-yl)-4-(1H-imidazol-4-yl)butan-2-one
0.015
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.18 Brucella suis (3S)-3-amino-4-(1H-imidazol-4-yl)-1-(4-methylphenyl)butan-2-one
0.018
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.9 Brucella suis methyl (7S)-5-sulfanylidene-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate
0.074
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.11 Brucella suis 2-(4-chlorophenyl)-1-[(7S)-5-sulfanylidene-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidin-7-yl]ethan-1-one
0.086
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.7 Brucella suis (7S)-7-[([1,1'-biphenyl]-4-yl)acetyl]-7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one
0.092
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.4 Brucella suis (7S)-7-[(4-chlorophenyl)acetyl]-7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one
0.095
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.12 Brucella suis 2-(4-methylphenyl)-1-[(7S)-5-sulfanylidene-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidin-7-yl]ethan-1-one
0.095
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.13 Brucella suis 2-(2,4-difluorophenyl)-1-[(7S)-5-sulfanylidene-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidin-7-yl]ethan-1-one
0.098
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.3 Brucella suis (7S)-7-[(4-bromophenyl)acetyl]-7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one
0.105
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.10 Brucella suis 2-(4-bromophenyl)-1-[(7S)-5-sulfanylidene-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidin-7-yl]ethan-1-one
0.113
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.5 Brucella suis (7S)-7-[(4-methylphenyl)acetyl]-7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one
0.143
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.6 Brucella suis (7S)-7-[(2,4-difluorophenyl)acetyl]-7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one
0.175
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.8 Brucella suis (7S)-7-[[4-(7-phenylhept-1-yn-1-yl)phenyl]acetyl]-7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one
0.322
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.15 Brucella suis 2-[4-(7-phenylhept-1-yn-1-yl)phenyl]-1-[(7S)-5-sulfanylidene-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidin-7-yl]ethan-1-one
0.532
-
at 30┬░C in the presence of 0.05 mM histidinol, 2 mM NAD+ and 0.5 mM MnCl2 in 150 mM sodium glycine buffer at pH 9.2 Brucella suis methyl (7S)-5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidine-7-carboxylate